In my experience flights are usually a little cheaper as well during the week.....

We prefer weekday flights because the airport is less crowded.

I book whatever day I find the cheapest flight, and like dustmon said, it's usually a weekday, and specifically have had better luck with Tuesday and Wednesday departures.

"Also thinking it may be less crowded checking in and out if we arrive on a weekday."

Most people who work a standard 9 to 5 job normally find that it is better to arrive and depart on Sat. or Sun. as that fits their work schedule better. Weekend arrivals/departures also work better with families with school age children. This general rule has been true at all Jamaican resorts I have ever stayed at. While some people arrive/depart every day of the week, you will find check-in shorter as a rule on a weekday but I do not normally find that to be a major issue. If you can be flexible then I would consider price, for both air and land, to be more important in deciding when to arrive and depart.

In our many travels to Negril, we travel mid week to mid week and book far enough in advance to get great deals both in hotel and airfare plus with airfare we have a good seat selection. As for MBJ, when you arrive, the midweek is less congested as the weekends when most people travel....sometimes, not always but if we had a choice we would always pick mid week travel, Vinnie makes a good point also.

We always do a Friday. Since we live in Nevada, that still gives us the weekend to get home and recover from the time change and to "face reality"

Usually a Tue. or Wed. is the best. Just from personal experience.

We do Friday to Friday. Thus giving us the weekend to get reacquainted with reality :)

BarbML, also be sure that you visit the Couples message board, there are meet up threads for each of the resorts. You will find a lot of folks that will be at CSS the same time that you will be.